Isn't that the Baker from SS14? I would not over think it -- it is a very easy jacket to wear. Wear it with any casual outfit...t-shirt or popover with any type of EG trouser...trainers or casual shoes.
I just searched old threads, which seem to say that the RLPL Made in Italy shoes are made by Silvano Sassetti. So not sure if this still applies or they are now made by Lattanzi.
Do people have any experience with the RLPL Made in Italy shoes in any case? Can anyone comment? I know the retail on the boots is $1500, but let's assume they are purchased at a deep discount.